Major Money: Rappers Who Signed Million-Dollar Deals

So who’s really breaking the bank in the industry? We take a look at a list of rappers who have signed multi-million or million dollar record deals. Some may take you by surprise, while others seem to fit the slot perfectly…

What most music fans don’t know is that a major record label deal is not guaranteed change in your pocket. A recording contract is essentially a legal agreement which allows the record label to exploit an artist’s work through recorded material. This includes the album’s release, promotion, marketing, sales… you name it. The price tag set on the deal merely highlights the label’s potential investment, not necessarily the artist’s income.

A lot of up-and-coming artists are now ditching their life long dreams of being signed to a major record label. They are ready to create their own situation. It seems like independent artists such as Chance The Rapper and Macklemore & Ryan Lewis are breaking the norm and setting a new stage for success.

With that being said, we compiled a list of the biggest rap deals in rap history, in no particular order. While there are many success stories, there are some unfortunate fails as well.

Kreayshawn - 1 Million

“Gucci Gucci, Louis Louis, Fendi Fendi, Prada. The basic bitches wear that shit, so I don't even bother.” Coming out of Oakland, CA, female emcee Kreayshawn is responsible for this track titled “Gucci Gucci,” which went viral after hitting the Internet. This landed her a one million dollar recording contract with Columbia Records, which is part of Sony Music Entertainment. The signing took place in June 2011, with the release of her debut album following one year later.

Meanwhile, all glamour aside, when rumors of this million dollar deal surfaced, Kreayshawn was bombarded with people asking her for money. Having a strong grip on how the music industry worked, she knew she had to be extra careful with her money from that point forward.

“You don’t even get half of it right away and then you got all these things to pay off and then you gotta upgrade your whole lifestyle yourself,” Kreayshawn states, as per rapfix.mtv.com. “You never know, I could be calling you back for some money, like, ‘Remember that interview we did? Can I get a job?’”

Chief Keef - 6 Million

At just 17 years of age, Chicago-bred Chief Keef caused a stir in the rap industry by signing a multi-million dollar deal with Interscope. Rising above some of hip-hop’s greats, this teenage gangster rapper was given the opportunity to gain 6 million dollars over three years and three albums. This also included a separate deal for Chief to control his own record label, which he named Glory Boyz Entertainment.

Being a minor, court approvals were required for the finalization of the contract. Interscope gave him $440,000 up front, and the rest would be given after the court’s approval. While Chief was not be able to indulge in this big time paycheck until he reached the age of 18, he may be Finally Rich, which is the name of his first studio album. However, this is all contingent on the success of his future album sales…

Trinidad James - 2 Million

Thanks to Trinidad James, “All Gold Everything” had everybody hyped up at one point or another. The popularity of the song drew a lot of attention to the rap rookie, particularly from the legendary hip-hop label Def Jam. Sadly, this is as far as the Atlanta rapper went. His career never set sail after the viral hit. On August 2, 2014, he announced via Twitter that Def Jam had decided to part ways with him.

“I should tell yall. I got dropped by the Label. My Album is now free. If u hear ur beat or verse on it. I hope u want dap cuz i got no money.” -Trinidad Jame$ (@TrinidadJamesGG)

A$AP Rocky - 3 Million

Also emerging on top in the rap industry, A$AP Rocky’s multi-million dollar deal with Polo Grounds Music, a subdivision of Sony/RCA, is one of the largest deals to this day. Unlike most up-and-coming artists who decide to remain independent, New York rapper A$AP Rocky decided to sign the deal while he was just fresh in the scene. When asked what led him to sign the agreement so quickly, his response was simply the three million dollars.

“I’m going to have creative control; there's no bullshit. The situation is almost unrealistic. I mean, five months ago I had about $3,000 in my bank account. Now I'm worth $3 million. Nobody's gotten a deal like that since 50 Cent,” A$AP Rocky stated, as per pitchfork.com.

Rakim - 1 Million

One of hip-hop’s all-time greatest emcees, Rakim takes the role as the first rapper to have a million dollar record deal. Alongside his partner Eric B, the New York hip-hop duo set the bar high for every DJ/emcee combo to come. During a time where many artists were getting ripped off dealing with record companies taking advantage of them, R and Eric signed a million dollar contract with MCA.

Even Nas acknowledges this in his track U.B.R (Unauthorized Biography of Rakim), stating “First million-dollar deal ever in rap, 18th Letter did that.” Besides Rakim referring to himself as the R, he also has an album called The 18th Letter.

Drake - 2 Million

The dude in the wheelchair in the TV show "Degrassi" has undoubtedly taken over the music scene. In line with his recent single “Started From The Bottom,” Canadian sensation Drake was basically a nobody in the music scene at one point in time. With some outlandish marketing efforts and the help of his mentor, Lil Wayne, Drizzy proved himself with the success of his hit single “Best I’ve Ever Had.” The track rightfully takes the place of 2009’s “Song of the Summer,” taking over iTunes, YouTube, the Billboard charts, your playlist, his playlist… you get it.

While attracting the likes of many record labels, October’s Very Own signed a two million dollar contract with Aspire/Young Money/Cash Money, distributed by Universal. In addition to this advance, Drake is able to keep his publishing rights and only has to give up 25% of his revenue from music sales to the label as a “distribution fee.” In most cases, the artist signs a “360” deal where all their revenue, including their touring and merchandise, is shared with the label.

Nas - 3 Million

No surprise here, as hip-hop mogul Nas is among the list signing a 3 million dollar contract with Def Jam, with Jay Z as his boss. This marked the end of the longtime feud between Hov and God’s Son, which started in 2001. Jay Z was still the president of Def Jam when Nas signed the agreement in 2006. The deal granted the New York emcee a recording budget for each album he would put out.

Unfortunately, he did not live up to expectations, with his Hip Hop Is Dead and Untitledalbums only going gold. In addition to that, Nas’ divorce with ex-wife Kelis that was finalized in 2010 cost him about $44,000 in alimony payments. Either way, his undeniable talent will always be reflected through his music.

50 Cent - 1 Million

New York rapper 50 Cent, also the leader of G-Unit, landed a million dollar contract with Shady Records/Aftermath Entertainment. After being released from Columbia where he had received a $65,000 advance, 50 started selling his music to bootleggers. This turned out to work to his advantage, as he gained the attention of many, including Eminem, who later announced that 50 Cent was his favorite rapper on a Los Angeles radio show.

Before Eminem decided to bring 50 Cent onto his label, they partook in a rap battle to see if 50 was worthy. Eminem took the win, although 50 claims it’s only because Em made him go first. His first single for Aftermath was “Wanksta,” which was on tracklist for the "8 Mile" soundtrack. With the release of his movie, “Get Rich or Die Tryin’,” 50 Cent represents a true emcee who lives hip-hop in his lifestyle as much as his music.

Jay Z - 150 Million

Leave it to Jay Z to land the most profitable contract in rap history -- a 150 million dollar contract with Live Nation. Departing from Def Jam records in 2008, the A-list recording artist follows in the footsteps of Madonna, who signed a 10 year, $120 million dollar deal the year prior. The deal includes money for many business ventures including a label, music publishing, and management services.

There is no denying that Hov is one of the nation’s most successful artists and entrepreneurs. Selling over 75 million records to this day and being the co-creator of the clothing line Rocawear, he is truly “Big Pimpin'.”

Odd Future - 2.5 Million

Led by Tyler the Creator, Odd Future Wolf Gang Kill Them All is a rap collective stemming from Los Angeles, California. Members include emcees Hodgy Beats, Domo Genesis, Mike G, Earl Sweatshirt, R&B sensation Frank Ocean, and producers Left Brain, Syd Tha Kyd, and many more. This young group proves how epic it is to be able to make music with your closest homies, as portrayed in their TV show, Loiter Squad.

In April of 2011, Odd Future signed a contract with RED Distribution in hopes of starting their new label. RED is the sales and marketing division of Sony Music that deals with independent artists. This led to the creation of Odd Future Records, with all business decisions made under this distribution.

Papoose - 1.5 Million

Brooklyn rapper Papoose got his break in the rap industry in 2005 with his track “Alphabetical Slaughter.” This led to the signing of a 1.5 million dollar deal with Jive Records. However, his career never seemed to take off like he had hoped. Failing to produce a hit single or a major studio album, Jive decided to drop the emcee from their label. To keep his name alive, Papoose released over 12 free mixtapes in the following years. He was awarded Mixtape Artist of the Year at the Justo’s Mixtape Awards in 2005.

Jim Jones - >1 Million

Original member of the hip-hop collective The Diplomats (Dipset), New York rapper Jim Jones comes out on top as he lands a multi-million dollar contract with Sony Records. In an exclusive interview with Miss Info, he states, “I just left the lawyer’s office. I signed a multi-million dollar joint venture with Sony. My boss is Rick Rubin, and Hip Hop [Kyambo Joshua, former Roc-A-Fella Records A&R] is doing my albums with me. What you think Jay-Z is gonna think about that?”

Alongside childhood friend Cam’ron, another member of Dipset, he also co-founded Diplomat Records. His breakthrough single “We Fly High” hit number five on the Billboard Hot 100.